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For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

Tucked in the Rainforest of Costa Rica is this incredible Ecolodge. We whitewater rafted all morning to arrive at the lodge, our river guides acted as chefs and general grounds keepers upon arrival, and we were treated to the absolute best food we had the entire trip in Costa Rica. The bungalows do not have any electricity, but the staff lights candles in all the rooms and pathways each evening, and dinner is eaten by candle light. Talk about romance!! While staying they have horseback riding through the jungle, hikes, rappelling, zip lining and of course more rafting. Definitely will not be our last trip to this lodge!! The attention to sustainability efforts was also fantastic and commendable.

Active from the 13th to 15th centuries and considered an influence on the pre-Renaissance movement, the Sienese School of painting is identifiable by its themes—always religious, and usually with a focus on Biblical miracles—and its signature style, a dreamy mix of Roman, Gothic, and Byzantine influences that often feature dazzling gold backgrounds. Opened in 1932, this museum boasts one of the world’s largest collections of Sienese School works, as well as a number of Renaissance and late-medieval pieces from Italian artists. Wander through the impressive building—a combination of two 14th- and 15th-century noblemen’s palazzi—to find works like Duccio’s Madonna and Child, Michelino da Besozzo’s Mystical Marriage of Saint Catherine (celebrating the “calling” of Siena’s native daughter), and Bartolo di Fredi’s expansive Adoration of the Magi. Paired with a visit to Florence’s Uffizi, coming here offers insight into the differences—and longtime rivalry—between the two cities.

Established in 1800, the Library of Congress is the oldest federal institution in the United States. The library was destroyed by British troops just 14 years after its conception, and Congress used Thomas Jefferson’s collection of 6,487 volumes to replace it. Today, the collection of the Library of Congress—housed across three buildings—grows by approximately 12,000 items a day and is the second largest library in the world with 164 million items and 838 miles of shelves (that’s farther than the distance from Washington, D.C. to Chicago!). The library holds the world’s largest collection of comic books and one of only three remaining Gutenberg bibles. The Library of Congress offers daily guided tours to explore its historic collection and famous Beaux-Arts architecture.—Miranda Smith

There are few better places from which to enjoy river views and sunsets than the Ponte Vecchio, built in 1345. Spanning the Arno’s narrowest point, this is the only bridge to have survived the German bombing of the city in 1944. There have always been shops on the bridge; the original butchers and grocers were replaced by sweeter-smelling gold and silversmiths in 1593. Sitting right in the middle is a bust of Benvenuto Cellini (1500-1571), the most famous goldsmith of them all.

This light-filled adobe space, which opened to the public in late 2017, is dedicated to encaustic art. Encaustic, which means “to burn or heat” in Greek, is the result of mixing colored pigments into heated beeswax and resin before applying to a surface with a brush or tool. Because the wax has body, it can be sculpted into shapes as well as painted and layered onto a canvas. The nonprofit gallery has over 300 encaustic works on display, most of which are for sale (70 percent of each sale goes directly to the artist).

This shopping plaza restaurant—set in the chilled-out, North Shore surf town of Hale‘iwa—evokes deeply nostalgic, yearning sighs from big-city folks. It is, quite possibly, the state’s best Thai food. But be prepared for cash only, erratic opening hours, no reservations, massive queues, lengthy waits for food once seated, and a highly variable menu. The chef-owner Opal quizzes patrons about their preferences... and then starts cooking. Man, are the results ever worth any slight inconveniences! Too hungry to wait? Stroll 0.2 miles north to tasty Rajanee Thai, which has a small dining room, as well as a takeaway window and outdoor picnic benches. Like many North Shore eateries, both establishments are BYOB: Long Drugs across from Opal sells adult beverages.

There’s a carefree summer camp spirit at Ruschmeyer’s, a boutique retreat in Montauk where a central garden full of hammocks and picnic tables creates a relaxing backdrop. First built in 1952 in a shaded stretch of lakeside woodlands in Montauk, the hotel now features recently renovated rooms inspired by camp cabins with cedar-plank walls, a hammock, and some with an outdoor charcoal grill. Ruschmeyer’s has an appetite for culture, seen in a rotating series of music performances, guest DJs, and artists-in-residence. This is a place to play, and the hotel happily arranges paddle boarding, fishing, and yoga. Start your stay on the central lawn, called the Magic Garden, with a game of ping-pong before drinking and dancing the night away at the hotel’s bar, the Electric Eel.

Just when it seemed like the Riviera Maya Riviera had become nothing but a sea of all-inclusive beach resorts, you stumble upon the quaint little Mexican village of Puerto Morelos. There are almost no huge developments, no shopping outlets, and no chain restaurants. The place is absolutely magical and is like traveling back in time. There is a small town square or plaza lined with palm trees, small cafes, and local boutiques. You can always find a good margarita to sip on at the super hip little bars scattered around the small town. If you find yourself on the Yucatan peninsula don’t miss this opportunity to travel back in time 50 yrs and experience the “old” Mexico.

This beautiful one-mile stretch was donated to the people of the Virgin Islands by Arthur Fairchild, a benefactor of the islands who’d made his fortune on Wall Street before retiring here. The usually calm waters of the heart-shaped bay make the beach the most popular on St. Thomas. Rent beach chairs and floats, and pick up lunch from stands selling burgers, pizza, and other snacks. Lifeguards are on duty every day.

The Coronado Bridge links San Diego to Coronado Island—and the present to the past. In the span of just 2.12 miles, you’ll travel from the digital age to a century when “electrified” hotels were practically unheard of. When the Hotel Del Coronado debuted in 1888, its electric lights and telephones made a sensation—as did its resplendence. In 1892, a young guest named Noel proclaimed in a letter to her family back east that “the red and the white between the bluest sky and the bluest water is like a beautiful dream in a fairy story.” Legions of A-listers have checked in ever since, as a who’s who of vintage portraits attests. But while a stay here is delightfully nostalgic—featuring bike rentals, beachside cabanas, and evening clambakes—the 757-room hotel doesn’t live entirely in the past. Take advantage of its upscale spa, spin classes on the beach, and restaurants serving updated takes on coastal cuisine along with creative cocktails. In the historic Victorian Building Suites, you’ll find modern coastal-chic interiors, streaming TVs, and, of course, Wi-Fi. The Beach Village Suites include additional modern luxuries—like a Sub-Zero fridge and dedicated concierge to help you fill it.

Aptly named Subsix sits six meters (almost 20 feet) below the water’s surface at Per Aquum’s Niyama resort, reached by speedboat (and then a three-tier staircase that descends into the sea). The ocean-inspired decor complements the underwater surroundings, where guests sip gin-infused cocktails like the Swing ’n’ Swim while admiring coral reefs and keeping an eye out for the likes of parrot fish, eels, and turtles. Lunch is a four-course set menu, featuring chef creations like lobster medallions with heirloom tomatoes and blackberry essence, or swimmer crab accompanied by couscous pomelo and ocean foam. You can also arrange for a private dinner or champagne breakfast, and for those with energy to burn, Subsix hosts twice-weekly “glow party” club nights.

Austinites had seen pizzas come in square or rectangular shapes before brothers Brandon and Zane Hunt arrived from Michigan, but they may not have associated the style with Detroit. Cooked in replicas of metal pans used on automotive assembly lines, these thick pies have a cheesy layer that extends to the edge of each slice. The Detroiter features two types of pepperoni, one smoked and one natural casing, mixed with a layer of cheese, atop tomato sauce, with some of the curled cups of pork riding to the surface of the slice. The brothers started with one pizza trailer and have since expanded to two brick-and-mortar locations and added a second trailer.

Comprised of just 10 suites with distinctly different designs, Palácio Belmonte feels more like a dream vacation home than a hotel. The vibe is spot on, given the backstory: A Frenchman traveled to Lisbon looking for a vacation home in the Portuguese capital. He first saw the building from a taxi and thought to himself, “It has nine windows, just like my home in France. I’ll buy it.” It wasn’t until after purchasing the property that he actually set foot inside and saw just how enormous it was—far too large for him and his family. Thus, he set about remodeling the building (which was originally owned by a noble family in the 1400s) with the notion of converting it into a space for visitors.

Quiet, hidden beaches that once defined the Caribbean are still favored by discriminating travelers. Serene and blessed with a few basic facilities (including parking, restrooms, and changing areas, as well food trucks), Brewers Bay Beach offers visitors an easily accessed, languid, sweeping shore. It’s an ideal spot for grabbing a towel, relaxing, and watching the sun set. With shallow, calm, clear, and reef-protected waters, the beach is popular with families, who can enjoy the gentle surf. Snorkeling is also popular, and the beach is home to stingray and turtle communities. Despite its secluded feel, Brewers Bay Beach is located near the University of the Virgin Islands campus and Cyril E. King International Airport.